benzhydryl (6R,7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-trityloxyiminoacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate → benzhydryl (6R,7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-trityloxyiminoacetyl]amino]-8-oxo-3-sulfanyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 2288048Notes

Reaction equation

HRID 2288048 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:57])[C@@H:24]([NH:25][C:26](=[O:56])/[C:27](/[C:49]4[N:50]=[C:51]([NH2:55])[S:52][C:53]=4[Cl:54])=[N:28]\[O:29][C:30]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)C4C=CC=CC=4)[C@H:21]3[S:20][CH2:19][C:18]=2Cl)=[O:16])C2C=CC=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[SH2:60].[Na].P(O)(O)([O-])=O.[Na+]>CN(C=O)C>[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:57])[C@@H:24]([NH:25][C:26](=[O:56])/[C:27](/[C:49]4[N:50]=[C:51]([NH2:55])[S:52][C:53]=4[Cl:54])=[N:28]\[O:29][C:30]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C@H:21]3[S:20][CH2:19][C:18]=2[SH:60])=[O:16])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 10581389benzhydryl (6R,7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-trityloxyiminoacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 23672064Monosodium phosphateHCID 53442613Sodium hydrogen sulfide hydrate

Product 1

HCID 141584533benzhydryl (6R,7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-trityloxyiminoacetyl]amino]-8-oxo-3-sulfanyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 190.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino)acetamido]-3-chloro-3-cephem-4-carboxylate diphenylmethyl ester (4.0 g, 4.72 mmol) in DMF (30 mL) cooled to -20° C. was added in one portion powdered sodium hydrogen sulfide hydrate (1.1 g, 19.6 mmol). After 15 min the reaction mixture was poured into 0.5M monosodium phosphate (about 100 mL), extracted with ethyl acetate and the organic layer was washed thoroughly with water. After concentrating in vacuum the crude title product was obtained as yellow foam 3.8 g (95%). 1H NMR (CDCl3 /CD3OD) δ 3.38 (d, 1H, J=15), 4.43 (d, 1H, J=15), 5.03 (d, 1H, J=5), 5.80 (d, 1H, J=5), 5.99 (br s, 1H), 6.80 (s, 1H), 7.05-7.50 (m, 25H).

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer was washed thoroughly with water
  3. concentrationAfter concentrating in vacuum the crude title product

Sources & evidence

ORD record
ord-a67c1a35e8e94fe9ad45254fcf542382
Source dataset
uspto-grants-2000_07
Patent number
US06087355

Reaction notes

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